Maybe my age (or lack of it, at 34) colors how I perceive the high end. I didn't grow up drooling over the big silver face recievers, and wasn't around for the transition from tube to SS. So my various systems have no allegience to time. I buy a lot of vintage because I prefer things with history to them, and it's more affordable, and because I'd rather have 20 pairs of great speakers than 1 pair of absolutely jaw dropping amazing speakers. But a great system can have pieces in it from any one of the last 5 or 6 decades and sound fantastic to me. It's great to have so much to choose from.
I did hear a $3500 pair of speakers the other day that made me think, though, that if I bought them I wouldn't have to have a house full of wood boxes to trip over. It was a nice thought for a moment. I got to talk to the designer and after realizing how much time he had spent on them, and seeing as how they were the culmination of his couple of decades designing speakers, and knowing a little bit about how costs of many things only decrease when they are mass produced (which these weren't, yet)..that high price really doesn't seem that high.
At age 27 I'm in a very similar situation. I appreciate vintage audio equipment, and I own a Thorens TD125 MKII, but I've chosen to buy a lot of new gear. I love pretty much everything I have, but I definitely understand the theme of this thread and have experienced it myself.
It's kind of difficult to put musicality into words, even though it's apparently (and rightly, IMO) considered the most important aspect of an audio system. To summarize musicality I usually just say that something (a CDP, turntable, whatever) breathes life into the music, while something else sounds analytical, sterile, too cold, etc.
I
have learned that the more expensive component is certainly not necessarily the better one, and in fact I'm experiencing that this very moment. Back in February I began listening to headphones much more in the evening, so I decided it would be good to invest in something better than the Grado SR-60 headphones I was using. I purchased the Grado 325i headphones at more than three times the price of the SR-60's. At first I loved them - after all, technically speaking they are better than the SR-60's in the areas of frequency extension, definition, inner detail, and soundstage. Unfortunately they've broken on me, and about four days ago I sent them back to Grado Labs to be repaired. So it's back to the SR-60's, this time with improved headphone pads that I originally bought for the 325i's. Over the last few days I've come to the somewhat startling realization that I
enjoy the SR-60's more than the 325i's! They're warmer, there's simply more bass, and the music sounds more personal and alive, if you will.
This is just what came to my mind when I read this thread, the point being that better is not always the best.

Of course I'm talking about equipment that's waaay less expensive than the original quote of the thread, but the idea is the same.
Great topic Erik, and timely for me as well.
Dave